JP2011524448A - ポリオールの製造方法 - Google Patents
ポリオールの製造方法 Download PDFInfo
- Publication number
- JP2011524448A JP2011524448A JP2011513908A JP2011513908A JP2011524448A JP 2011524448 A JP2011524448 A JP 2011524448A JP 2011513908 A JP2011513908 A JP 2011513908A JP 2011513908 A JP2011513908 A JP 2011513908A JP 2011524448 A JP2011524448 A JP 2011524448A
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- product
- polyol
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- hour
- koh
- Prior art date
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- Granted
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- 229920005862 polyol Polymers 0.000 title claims abstract description 44
- 150000003077 polyols Chemical class 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000004814 polyurethane Substances 0.000 claims abstract description 9
- 229920002635 polyurethane Polymers 0.000 claims abstract description 9
- -1 ester polyols Chemical class 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 60
- 239000003054 catalyst Substances 0.000 claims description 40
- 239000007858 starting material Substances 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 19
- 238000006386 neutralization reaction Methods 0.000 claims description 17
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 239000012467 final product Substances 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 14
- 229920000570 polyether Polymers 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 93
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
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- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- 150000001412 amines Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical class CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical class OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical class OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Chemical class CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Chemical class 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical class CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical class NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical class OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 235000019512 sardine Nutrition 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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Abstract
Description
Irganox(登録商標)1076:オクタデシル3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート
10Lの実験用オートクレーブ中に、窒素雰囲気下で、1046.1gのエチレンジアミンを導入した。充填ノズルを閉じた後、3barの窒素圧を3回かけて残留酸素を除去し、その後、余分な圧力を大気圧まで下げた。攪拌(450rpm)しながら150℃に加熱し、3711.5gのプロピレンオキシドをオートクレーブ中に3時間かけて計量添加した。次いで、その混合物を1時間反応させた後80℃に冷却した。44.82重量%のKOH水溶液2.815gを添加した後、150℃、真空(20mbar)において、窒素(50ml/分)で除去することにより、水を1時間かけて留去した。次いで、1244.2gのプロピレンオキシドを2.5時間かけて計量添加した。続く後反応時間は、1.5時間であった。真空で30分加熱し室温まで冷却した後、中和試験(実施例1Aおよび1B)用に2留分をバッチより取り出した。触媒濃度(KOH)は210ppmであった。
2.028gの11.82%硫酸(KOH1モルあたり硫酸0.50モルに相当)を、80℃で、実施例1の生成物1305.2gに添加し、80℃で1時間攪拌した。0.88gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
4.064gの11.82%硫酸(KOH1モルあたり硫酸1.00モルに相当)を、80℃で、実施例1の生成物1307.6gに添加し、80℃で1時間攪拌した。0.885gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
10Lの実験用オートクレーブ中に、窒素雰囲気下で、1049gのエチレンジアミンを導入した。充填ノズルを閉じた後、3barの窒素圧を3回かけて残留酸素を除去し、その後、余分な圧力を大気圧まで下げた。攪拌(450rpm)しながら150℃に加熱し、3735gのプロピレンオキシドをオートクレーブ中に3時間かけて計量添加した。次いで、その混合物を1時間反応させた後80℃に冷却した。44.82重量%のKOH水溶液6.922gを添加した後、150℃、真空(20mbar)において、窒素(50ml/分)で除去することにより水を1時間かけて留去した。次いで、1252.2gのプロピレンオキシドを1時間かけて計量添加した。続く後反応時間は、1.5時間であった。真空で30分加熱し室温まで冷却した後、中和試験(実施例1Aおよび1B)用に2留分をバッチより取り出した。触媒濃度(KOH)は510ppmであった(実施例2A、2B、2C、2Dおよび2E)。
4.509gの11.82%硫酸(KOH1モルあたり硫酸0.51モルに相当)を、80℃で、実施例2の生成物1183.5gに添加し、80℃で1時間攪拌した。0.792gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
8.971gの11.82%硫酸(KOH1モルあたり硫酸1.00モルに相当)を、80℃で、実施例2の生成物1179.3gに添加し、80℃で1時間攪拌した。0.799gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
1.238gの85%リン酸(KOH1モルあたりリン酸0.99モルに相当)を、80℃で、実施例2の生成物1192.8gに添加し、80℃で1時間攪拌した。0.814gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。濁った生成物が得られた。
110mlの蒸留水と4.426gの11.87%硫酸(KOH1モルあたり硫酸0.50モルに相当)を、80℃で、実施例2の生成物1189.7gに添加し、80℃で1時間攪拌した。0.797gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。Pall社製のT750ディープベッドフィルターを備えた実験用吸引フィルターにてろ過後、透明な生成物が得られた。
106mlの蒸留水と8.819gの11.87%硫酸(KOH1モルあたり硫酸0.99モルに相当)を、80℃で、実施例2の生成物1182.4gに添加し、80℃で1時間攪拌した。0.790gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。Pall社製のT750ディープベッドフィルターを備えた実験用吸引フィルターにてろ過後、透明な生成物が得られた。
10Lの実験用オートクレーブ中に、窒素雰囲気下で、1025.2gのエチレンジアミンを導入した。充填ノズルを閉じた後、3barの窒素圧を3回かけて残留酸素を除去し、その後、余分な圧力を大気圧まで下げた。攪拌(450rpm)しながら150℃に加熱し、3725.7gのプロピレンオキシドをオートクレーブ中に3時間かけて計量添加した。次いで、その混合物を1時間反応させた後80℃に冷却した。44.82重量%のKOH水溶液13.668gを添加した後、150℃、真空(20mbar)において、窒素(50ml/分)で除去することにより、水を1時間かけて留去した。次いで、1249.1gのプロピレンオキシドを1時間かけて計量添加した。続く後反応時間は、1.5時間であった。次いで、アルカリ性粗生成物を150℃でさらに30分、真空で加熱した。触媒(KOH)濃度は1020ppmであった。
9.969gの11.87%硫酸(KOH1モルあたり硫酸0.50モルに相当)を、80℃で、実施例3の生成物1327.4gに添加し、80℃で1時間攪拌した。0.891gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
19.532gの11.87%硫酸(KOH1モルあたり硫酸1.00モルに相当)を、80℃で、実施例3の生成物1299.8gに添加し、80℃で1時間攪拌した。0.891gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。透明な生成物が得られた。
10Lの実験用オートクレーブ中に、窒素雰囲気下で、756.8gのエチレンジアミンを導入した。充填ノズルを閉じた後、3barの窒素圧を3回かけて残留酸素を除去し、その後、余分な圧力を大気圧まで下げた。攪拌(450rpm)しながら150℃に加熱し、2769.8gのプロピレンオキシドをオートクレーブ中に3時間かけて計量添加した。次いで、その混合物を1時間反応させた後80℃に冷却した。44.83重量%のKOH水溶液6.967gを添加した後、150℃、真空(20mbar)において、窒素(50ml/分)で除去することにより、水を1時間かけて留去した。次いで、2476.4gのプロピレンオキシドを1時間かけて計量添加した。続く後反応時間は、2時間であった。次いで、アルカリ性粗生成物を150℃でさらに30分、真空で加熱した。触媒濃度(KOH)は520ppmであった。
1.4325gの85%リン酸(KOH1モルあたりリン酸0.99モルに相当)を、80℃で、実施例4の生成物1347.8gに添加し、80℃で1時間攪拌した。0.911gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。濁った生成物が得られた。
118mlの蒸留水と4.934gの11.87%硫酸(KOH1モルあたり硫酸0.49モルに相当)を、80℃で、実施例4の生成物1303.8gに添加し、80℃で1時間攪拌した。0.881gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。 Pall社製のT750ディープベッドフィルターを備えた実験用吸引フィルターにてろ過後、透明な生成物が得られた。
118mlの蒸留水と、9.892gの11.87%硫酸(KOH1モルあたり硫酸0.99モルに相当)を、80℃で、実施例4の生成物1301.6gに添加し、80℃で1時間攪拌した。0.883gのIrganox(登録商標)1076を添加した後、生成物を18mbar(ウォータージェット真空)で1時間、その後、110℃、1mbarで3時間かけて脱水した。 Pall社製のT750ディープベッドフィルターを備えた実験用吸引フィルターにてろ過後、透明な生成物が得られた。
Claims (6)
- 最終生成物の量に基づいて0.004〜0.1重量%濃度の、アルカリ金属水酸化物、アルカリ金属水素化物、アルカリ土類金属水素化物、アルカリ金属カルボン酸塩、アルカリ土類金属カルボン酸塩またはアルカリ土類水酸化物に基づく触媒の存在下で、アルキレンオキシドをアミノ基含有出発化合物へ、塩基触媒を用いた付加を行うことによるポリオールの製造方法であって、使用する触媒1モルあたり0.75〜1モルの硫酸でポリオールの中和を行う、ポリオールの製造方法。
- 生成した塩を分離しない、請求項1に記載の方法。
- 中和前および/または中和中および/または中和後に、ポリオールに基づいて2%〜20%の水を添加し、水を取り除いた後に塩を分離する、請求項1に記載の方法。
- アルキレンオキシドの付加前または付加中に、最終生成物の量に基づいて10〜80重量%のトリグリセリドを添加する、請求項1〜3のいずれかに記載の方法。
- 請求項1〜4のいずれかに記載の方法により得られるポリオール。
- 請求項1〜4のいずれかに記載の方法により得られるポリオールの、ポリウレタンの製造における使用。
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CN102585197A (zh) * | 2011-01-05 | 2012-07-18 | 辽宁科隆精细化工股份有限公司 | 环氧化物加成的方法以及碱金属及其盐用于该方法的用途 |
MX337785B (es) | 2013-02-22 | 2016-03-18 | Bayer Materialscience Ag | Procedimiento de preparacion de polioles de polieter. |
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CN101033285A (zh) | 2007-02-14 | 2007-09-12 | 南京红宝丽股份有限公司 | 采用菜籽油制备的软质聚氨酯泡沫塑料 |
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JPS5770124A (en) * | 1980-10-20 | 1982-04-30 | Dai Ichi Kogyo Seiyaku Co Ltd | Purification of polyether-polyol |
JPH0718070A (ja) * | 1993-04-05 | 1995-01-20 | Arco Chem Technol Lp | 高度にエステル化されたアルコキシル化ポリオール組成物の製造方法 |
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Publication number | Publication date |
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EP2291434B1 (de) | 2012-08-08 |
MX2010013859A (es) | 2011-02-24 |
BRPI0914792A2 (pt) | 2015-10-20 |
CN102066460B (zh) | 2013-11-13 |
US20110105714A1 (en) | 2011-05-05 |
DE102008028555A1 (de) | 2009-12-17 |
PT2291434E (pt) | 2012-10-23 |
ES2391534T3 (es) | 2012-11-27 |
CA2727743C (en) | 2016-01-19 |
EP2291434A1 (de) | 2011-03-09 |
PL2291434T3 (pl) | 2013-01-31 |
WO2009152954A1 (de) | 2009-12-23 |
KR20110029125A (ko) | 2011-03-22 |
JP5528437B2 (ja) | 2014-06-25 |
CA2727743A1 (en) | 2009-12-23 |
CN102066460A (zh) | 2011-05-18 |
US8501904B2 (en) | 2013-08-06 |
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